Jon Sabes - Sep 15, 2022 Form 4 Insider Report for FOXO TECHNOLOGIES INC. (FOXO)

Role: CEO, Chairman, Director, 10%+ Owner
Signature: /s/ Jon Sabes
Stock symbol: FOXO
Transactions as of: Sep 15, 2022
Transactions value $: $0
Form type: 4
Date filed: 9/16/2022, 09:38 PM

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	FOXO	Common Stock	Award		+373K			373K	Sep 15, 2022	By JK-JBM Family Investment LLC	F1, F2
transaction	FOXO	Common Stock	Award		+1.16M			1.16M	Sep 15, 2022	By FOXO Management, LLC	F1, F3
transaction	FOXO	Common Stock	Award		+3.51M			3.51M	Sep 15, 2022	Direct	F4

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	FOXO	Warrant	Award	$0	+182K		$0.00	182K	Sep 15, 2022	Class A Common Stock	182K	$6.21	By JK-JBM Family Investment LLC	F2, F3, F5
transaction	FOXO	Stock Option (right to buy)	Award	$0	+860K		$0.00	860K	Sep 15, 2022	Class A Common Stock	860K	$6.51	Direct	F6
transaction	FOXO	Stock Option (right to buy)	Award	$0	+2		$0.00	2	Sep 15, 2022	Class A Common Stock	2	$9.15	Direct	F7

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	In connection with the merger described in that certain Agreement and Plan of Merger, dated as of 2/24/2022 (as amended, the "Merger Agreement"), by and among FOXO Technologies Inc., formerly Delwinds Insurance Acquisition Corp. (the "Issuer"), DWIN Merger Sub Inc. ("Merger Sub"), and FOXO Technologies Operating Company, formerly FOXO Technologies Inc. ("FOXO"), pursuant to which Merger Sub merged with and into FOXO, with FOXO surviving as a wholly-owned subsidiary of the Issuer (the "Merger"). Pursuant to the terms and conditions of the Merger Agreement, in connection with the closing of the Merger on 9/15/2022 (the "Closing Date"), the reporting person received (i) 372,680 shares of Class A common stock in the Issuer to be held by JK-JBM Family Investment LLC and (ii) 1,161,674 shares of Class A common stock in the Issuer to be held by FOXO Management, LLC.
F2	Securities held of record by JK-JBM Family Investment LLC (the "LLC"). Jon Sabes is the manager of the LLC and is deemed to have sole voting and investment power over the securities held by the LLC.
F3	Securities held of record by FOXO Management, LLC ("FOXO Management"). Jon Sabes, is the sole voting member of FOXO Management and is deemed to have sole voting and investment power over the securities held by FOXO Management.
F4	In connection with the Merger, the reporting person received a restricted share award equal to 3,507,000 shares of Class A common stock of the Issuer pursuant to the terms and conditions of the FOXO Technologies Inc. Management Contingent Share Plan (the "MIP"). The restricted share award is subject to the following three service-based vesting conditions (i) 60% of the award will become vested on the 3rd anniversary of the Closing if the reporting person is still employed by the Issuer on such date, (ii) ) 20% of the award will become vested on the 4th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date, and (iii) the final 20% of the award will become vested on the 5th anniversary of the Closing Date if the reporting person is still employed by the Issuer on such date. In addition, 1/3 of the restricted share award will become vested upon the satisfaction of certain performance-based conditions as further described in the MIP.
F5	The warrant was received in exchange for a warrant to purchase 312,500 shares of FOXO Class A common stock in connection with the Merger. The warrant is immediately exercisable.
F6	The stock options were received in exchange for stock options to purchase 1,479,880 shares of Class A common stock of FOXO Technologies Operating Company ("FOXO") in connection with the merger of FOXO with and into a wholly owned subsidiary of the Issuer (the "Merger"), which closed on 9/15/2022 (the "Closing Date"). As of the Closing Date, 759,711.19 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 12/31/2023.
F7	The stock options were received in exchange for stock options to purchase 5 shares of Class A common stock of FOXO in connection with the Merger. As of the Closing Date, 0.39 of the shares of Class A common stock of the Issuer subject to the stock options were vested, and, thereafter, the remaining number of shares subject to the stock options shall vest in equal monthly installments until fully vested on 1/27/2025.